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Compound Detail

CHEMBL572

NITROFURANTOIN
💊 Approved Drug
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💊 Approved Drug
O=C1CN(/N=C/c2ccc([N+](=O)[O-])o2)C(=O)N1

Basic Information

ChEMBL ID CHEMBL572
Name NITROFURANTOIN
Phase Approved
Structure Type MOL
InChI Key NXFQHRVNIOXGAQ-YCRREMRBSA-N
Therapeutic ✓ Yes

Known Names

Berkfurin Ceduran Dantafur Furadantin Furalan Genfura Macrobid Macrodantin Nitrofurantoin Nitrofurantoin (monohydrate/macrocrystals) Nitrofurantoin anhydrous Nitrofurantoin component of macrobid +10 more
28
Targets
38
Activities
3
Assay Types
10
PK Parameters
20
Publications
22
Known Names
4
Indications
1
Mechanisms

Molecular Properties

238.2
MW (Da)
0.07
ALogP
6
HBA
1
HBD
118.0
PSA (Ų)
0.35
QED
0
Ro5 Violations
3
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1953
Availability Prescription
Chirality Achiral

Routes of Administration

Oral Parenteral

Flags

Natural Product
USAN Stem -toin

Extended Properties

Molecular Formula C8H6N4O5
MW 238.16
Aromatic Rings 1
Heavy Atoms 17
NP-Likeness -1.45

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
DNA inhibitor INHIBITOR DNA

Indications

Bacterial Infections Cystitis Urinary Tract Infections Osteomyelitis

ATC Classification

J01XE01
nitrofurantoin
Level 1: ANTIINFECTIVES FOR SYSTEMIC USE
Level 2: ANTIBACTERIALS FOR SYSTEMIC USE
J01XE51
nitrofurantoin, combinations
Level 1: ANTIINFECTIVES FOR SYSTEMIC USE
Level 2: ANTIBACTERIALS FOR SYSTEMIC USE

Activity Summary

IC50 27 meas. best 9.05
EC50 10 meas. best 6.16
Ki 1 meas. best 6.09

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Vero
CHEMBL391
IC50 9.05 9.05 0.9 1
Caco-2
CHEMBL614058
IC50 6.94 6.94 115.0 1
WI-38
CHEMBL614391
IC50 6.79 6.79 162.0 1
HeLa
CHEMBL399
IC50 6.78 6.78 166.0 1
Trypanosoma brucei rhodesiense
CHEMBL612348
IC50 6.3 6.3 500.0 1
Escherichia coli
CHEMBL354
EC50 6.16 5.43 690.0 2
CDGSH iron-sulfur domain-containing protein 1
CHEMBL1795168
Ki 6.09 6.09 816.0 1
Tumour suppressor p53/oncoprotein Mdm2
CHEMBL1907611
IC50 5.8 5.8 1580.0 1
A-427
CHEMBL614515
IC50 5.73 5.73 1860.0 1
Leishmania donovani
CHEMBL367
IC50 5.67 5.56 2120.0 2
NON-PROTEIN TARGET
CHEMBL3879801
IC50 5.63 4.77 2340.0 3
Streptococcus sp. 'group A'
CHEMBL612389
EC50 5.5 5.5 3161.0 1
Trypanosoma cruzi
CHEMBL368
IC50 5.36 5.36 4350.0 1
MCF7
CHEMBL387
IC50 5.35 5.35 4440.0 1
Streptokinase A
CHEMBL1293228
EC50 5.24 5.24 5825.0 1
DAN-G
CHEMBL614033
IC50 5.17 5.17 6740.0 1
RT-4
CHEMBL614884
IC50 5.16 5.16 7000.0 1
SISO
CHEMBL613527
IC50 5.14 5.14 7270.0 1
Streptococcus
CHEMBL612313
EC50 5.01 5.01 9830.0 1
CDGSH iron-sulfur domain-containing protein 1
CHEMBL1795168
IC50 4.72 4.72 19100.0 1
ATP-binding cassette sub-family C member 4
CHEMBL1743128
IC50 4.68 4.68 20900.0 1
5637
CHEMBL612565
IC50 4.67 4.67 21300.0 1
Staphylococcus aureus
CHEMBL352
EC50 4.57 4.57 27000.0 1
KYSE-510
CHEMBL613868
IC50 4.54 4.54 29000.0 1
Unchecked
CHEMBL612545
IC50 4.49 4.42 32209.0 3
Enterobacter cloacae
CHEMBL349
EC50 4.44 4.44 36000.0 1
Enterococcus faecium
CHEMBL357
EC50 4.42 4.42 38000.0 1
Klebsiella pneumoniae
CHEMBL350
EC50 4.4 4.4 40000.0 1
Unchecked
CHEMBL612545
EC50 4.33 4.33 47280.0 1
GroEL/GroES
CHEMBL4106139
IC50 4.08 4.08 84000.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 9.7 mL.min-1.kg-1 Homo sapiens
CL 9.7 mL.min-1.kg-1 Homo sapiens
CL 3.0 uL.min-1.(10^6cells)-1 Homo sapiens
F 80.0 % Homo sapiens
F 87.0 % Homo sapiens
Fu 0.17 - Homo sapiens
Fu 0.48 - Rattus norvegicus
Fu 0.4 - Homo sapiens
MRT 0.98 hr Homo sapiens
T1/2 0.97 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Vero IC50 = 0.9 nM 9.05 Anti-Herpes simplex virus type-1 activity in vero cells using plaque inhibition ... 10464017
Caco-2 IC50 = 115.0 nM 6.94 Anticancer activity against human Caco-2 cells incubated for 72 hrs by MTT assay 36921275
WI-38 IC50 = 162.0 nM 6.79 Cytotoxicity in human WI-38 cells assessed as reduction in cell viability incuba... 36921275
HeLa IC50 = 166.0 nM 6.78 Anticancer activity against human HeLa cells incubated for 72 hrs by MTT assay 36921275
Trypanosoma brucei rhodesiense IC50 = 500.0 nM 6.3 DNDI: HAT in Vitro, 72 hour -
Escherichia coli EC50 = 690.0 nM 6.16 Antibacterial activity against Escherichia coli assessed as reduction in bacteri... 33007545
CDGSH iron-sulfur domain-containing protein 1 Ki = 816.0 nM 6.09 Displacement of [3H]rosiglitazone from recombinant human C-terminal His-tagged M... 27687671
Tumour suppressor p53/oncoprotein Mdm2 IC50 = 1580.0 nM 5.8 Inhibition of human recombinant MDM2/p53 interaction measured after 10 mins by E... 36921275
A-427 IC50 = 1860.0 nM 5.73 Cytotoxicity against human A427 cells after 96 hrs by microtiter assay 18187237
Leishmania donovani IC50 = 2120.0 nM 5.67 DNDI: Leish (axenic) in Vitro, 72 hour -
NON-PROTEIN TARGET IC50 = 2340.0 nM 5.63 Cytotoxicity against human LCLC-103H cells after 96 hrs by microtiter assay 18187237
Streptococcus sp. 'group A' EC50 = 3161.0 nM 5.5 PUBCHEM_BIOASSAY: Luminescence Microorganism-Based Dose Confirmation HTS to Iden... -
Leishmania donovani IC50 = 3570.0 nM 5.45 Leishmanicidal activity against Leishmania donovani 9515 amastigote infected in ... 36516584
Trypanosoma cruzi IC50 = 4350.0 nM 5.36 DNDI: Chagas in Vitro, 96 hour -
MCF7 IC50 = 4440.0 nM 5.35 Cytotoxicity against human MCF7 cells after 96 hrs by microtiter assay 18187237
Streptokinase A EC50 = 5825.0 nM 5.24 PUBCHEM_BIOASSAY: Luminescence Microorganism-Based Dose Confirmation HTS to Iden... -
DAN-G IC50 = 6740.0 nM 5.17 Cytotoxicity against human DAN-G cells after 96 hrs by microtiter assay 18187237
RT-4 IC50 = 7000.0 nM 5.16 Cytotoxicity against human RT4 cells after 96 hrs by microtiter assay 18187237
SISO IC50 = 7270.0 nM 5.14 Cytotoxicity against human SISO cells after 96 hrs by microtiter assay 18187237
Streptococcus EC50 = 9830.0 nM 5.01 PUBCHEM_BIOASSAY: Luminescence Microorganism-Based Dose Response HTS to Identify... -

Literature References

Data from ChEMBL 36 via Core Engine